'When'

This all happened not too long ago. I just met this girl, Kirra. There was a group of us hanging out one friday night. It had gotten pretty late and we were all hanging out in a WalMart parking lot. Everyone else left to go hang out at someone's house, but Kirra didn't feel like going. I told her I'd stay and hang out with her.

We sat in her SUV for awhile talking. Eventually we put the seats down and laid down in the back. We talked for another hour or so when the conversation started to turn toward sex. I asked her if she had ever done it...

'Have you?' she asked. 'No, not yet. I mean, I'd like to someday soon, but not yet.' 'You masturbate don't you?' Kirra asked. 'Yeah, like, everyone does right?' I responded. 'Yeah I guess they do.' she said. It was getting a little serious so I though I'd inject some humor. 'There was this one time my friend told me about. They were all at his house playing 'When', when he-' 'Wait, what? 'When'?' She asked. 'Yeah, have you ever played 'When'?' 'No, what is that?' 'Well, there is different versions you can play, but normally you play it in a group, and everyone says when the last time they masturbated was. Then, whoever has gone the longest without masturbating has to do it in front of everyone.' I explained. 'Hm, never heard of that.' 'Neither did I till my friend told me about it.' 'So, Jake, when was the last time you masturbated?' she asked. 'Last night, why?' 'Ha! The last time I masturbated was this morning. That means you gotta do it in front of me!' I must admit, I was suprised. 'Whoa, wait, what? Hey, I never said I was playing!' 'Neither did I! But you lose either way!' she said. 'Come on, you gotta do it!' 'But, but-' I said. 'But nothing!' she said with a smile on her face. '*sigh* do you really want me to?' she nodded. 'Fine... Do you have any tissues?' I asked. 'Yep, right here.' she took some out of her purse. 'Alright...' I sighed. I laid down and she sat next to me holding the tissues.

I undid my belt and pushed my pants and boxers down around my ankles. Kirra pulled them off the rest of the way and put them in the front seat. Kirra took out a towel, unfolded it and placed it under my butt. 'So, what are you waiting for?' she asked. 'Alright, here I go.' And with that, I started to stroke my penis. This was the first time a girl had ever watched me do this, so it didn't take long to get close to orgasm. I started stroking fast and fast, and Kirra just sat their staring at me masturbate in fascination.

'Ok, I'm coming.' I said. Kirra grabbed my penis with one hand and positioned the tissues with her other. Not counting the first time I ejaculated back when I was 12, that was the greatest orgasm of my life. I just kept coming and coming. It felt like I had 100 contractions when it was all said and done. Kirra wiped off the head of my penis and threw the tissues on the floor. She wrapped the towel I was laying on around my waist and folded it in. She laid down next to me and kissed me on the cheek. 'Good job' she whispered into my ear. She placed a hand on my chest and we laid their silent. 'Kirra?' I asked. 'Yes?' 'When was the last time you masturbated?' She looked at me weird. 'There's this loophole in the game I forgot to mention...'